4'-Cyanoacetophenone → 1-(4-Cyanophenyl)3-dimethylaminopropen-1-one

HRID 1370072

Reaction equation

HRID 1370072 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[C:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1](=[O:3])[CH:2]=[CH:14][N:15]([CH3:17])[CH3:16])=[CH:5][CH:6]=1)#[N:9]

Participants

3

Reactant 2

HCID 740444'-CyanoacetophenoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 28059521-(4-Cyanophenyl)3-dimethylaminopropen-1-oneYield 62.3%

Procedure

A mixture of 4-acetylbenzonitrile (51.84 g, 0.357 mol) and N,N-dimethylformamide dimethyl acetal (142 ml, 1.07 mol) was heated to reflux for 1.5 h. The reaction was cooled to room temperature and the resultant crystalline mass collected by filtration and washed with diethyl ether (4×100 ml) to give 1-(4-cyanophenyl)-3-dimethylaminopropen-1-one as an orange solid (44.56 g). An additional crop of this product (11.40 g) could be obtained by partially concentrating the filtrate. δH (d6DMSO) 8.01 (2H, d, J 8.2 Hz), 7.87 (2H, d, J 8.2 Hz), 7.75 (1H, d, J 12.2 Hz), 5.83 (1H, d, J 12.2 Hz), 3.15 (3H, bs), 2.92 (3H, bs). MS (ESI) 201 (MH+, 100%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. filtrationthe resultant crystalline mass collected by filtration
  4. washwashed with diethyl ether (4×100 ml)

Sources & evidence

ORD record
ord-2a128117f5554bf5852dfff36040f838
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Linked notes

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